| 1997 | | | 1998 | |
| 103 | Hardin Brotherton (Virginia Episcopal) | | 103 | Mike Zubovnik (Blue Ridge) |
| 112 | Ryan Ingram (Norfolk Academy) | | 112 | Dave Hicks (St.Christopher's) |
| 119 | JJ Holmes (Blue Ridge) | | 119 | Bo Hurst (Collegiate) |
| 125 | Kyle Turner (Woodberry Forest) | | 125 | Gordon Kolb (Woodberry Forest) |
| 130 | Shaun Gehres (Blue Ridge) | | 130 | Mark Johnson (Collegiate) |
| 135 | John Gogos (Woodberry Forest) | | 135 | Shaun Gehres (Blue Ridge) |
| 140 | Cary Bowmer (St.Christopher's) | | 140 | John Gogos (Woodberry Forest) |
| 145 | Ben Clarke (Fork Union) | | 145 | Dustin Greene (Collegiate) |
| 152 | John McLeod (Collegiate) | | 152 | Maurice Wilson (Blue Ridge) |
| 160 | Randy Holmes (Blue Ridge) | | 160 | Jimmy Hovis (St. Christopher's) |
| 171 | Marvin McLain (Blue Ridge) | | 171 | Marvin McLain (Blue Ridge) |
| 189 | Garrett Mock (Woodberry Forest) | | 189 | Trey Harris (Woodberry Forest) |
| 215 | Trey Harris (Woodberry Forest) | | 215 | Andy Deck (Collegiate) |
| HWT | Andrew Bogle (St. Christopher’s) | | HWT | Peyton Studebaker (St.Christopher's) |
| 1999 | | | 2000 | |
| 103 | Steve Sica (Collegiate) | | 103 | Steve Sica (Collegiate) |
| 112 | Matt Anderson (Collegiate) | | 112 | Hunter Carpenter (St.Christopher's) |
| 119 | David Hicks (St.Christopher's) | | 119 | Charlie Moore (St.Christopher's) |
| 125 | Bo Hurst (Collegiate) | | 125 | Mike Kellam (Norfolk Academy) |
| 130 | Asher Rolfe (St.Christopher's) | | 130 | David Hicks (St.Christopher's) |
| 135 | Patrick Boswell (Collegiate) | | 135 | Ben Guerrina (Woodberry Forest) |
| 140 | Mark Johnson (Collegiate) | | 140 | Taino Ortiz (Woodberry Forest) |
| 145 | Dustin Greene (Collegiate) | | 145 | Leif Lindhjem (Norfolk Academy) |
| 152 | Reed Shelger (Woodberry Forest) | | 152 | Patrick Boswell (Collegiate) |
| 160 | Rhett Bennett (Woodberry Forest) | | 160 | Reed Shelger (Woodberry Forest) |
| 171 | Brian Burchette (Woodberry Forest) | | 171 | Earl Walker (Fork Union) |
| 189 | Jimmy Hovis (St.Christopher's) | | 189 | J.D. Patton (Woodberry Forest) |
| 215 | Andy Deck (Collegiate) | | 215 | Jimmy Hovis (St.Christopher's) |
| HWT | Charles Payne (Woodberry Forest) | | HWT | Charles Payne (Woodberry Forest) |
| 2001 | | | 2002 | |
| 103 | Zach Weisberg (Norfolk Academy) | | 103 | Joe Lawson (Collegiate) |
| 112 | Dan DeLalla (Norfolk Academy) | | 112 | Brian Herod (St.Christopher's) |
| 119 | Steve Sica (Collegiate) | | 119 | Jamie Robertson (Collegiate) |
| 125 | Mike Dulinawka (Fork Union) | | 125 | Dan Delalla (Norfolk Academy) |
| 130 | Mac Fridell (Collegiate) | | 130 | Mike Dulinawka (Virginia Episcopal) |
| 135 | Morgan Crocker (Blue Ridge) | | 135 | Hunter Macdonald (St.Christopher's) |
| 140 | Hunter Moore (Virginia Episcopal) | | 140 | Mac Fridell (Collegiate) |
| 145 | Ben Guerrina (Woodberry Forest) | | 145 | Ian Macdonald (St.Christopher's) |
| 152 | Neil Loughrie (Collegiate) | | 152 | Kirk Adamson (St.Christopher's) |
| 160 | Andrew Barber (Blue Ridge) | | 160 | Ryan Robertson (St.Christopher's) |
| 171 | Burton Fuller (St.Christopher's) | | 171 | Conner Gentil (Woodberry Forest) |
| 189 | Ted Zimmerman (Woodberry Forest) | | 189 | Brian McGurk (St.Christopher's) |
| 215 | Peter Knowles (St.Christopher's) | | 215 | Akel Grantham (St.Christopher's) |
| HWT | Mike Bregman (Blue Ridge) | | HWT | Seth Lotts (Collegiate) |
| 2003 | | | 2004 | |
| 103 | Grant Giordano (Norfolk Academy) | | 103 | Tyler Hamblen (St.Christopher's) |
| 112 | Brian Herod (St.Christopher's) | | 112 | Vinny Delalla (Norfolk Academy) |
| 119 | Thomas Nielsen (Woodberry Forest) | | 119 | Brian Herod (St.Christopher's) |
| 125 | Jamie Robertson (Collegiate) | | 125 | John Clore (Collegiate) |
| 130 | Hunter Carpenter (St.Christopher's) | | 130 | Jamie Robertson (Collegiate) |
| 135 | Dan Delalla (Norfolk Academy) | | 135 | David Schafer (St.Christopher's) |
| 140 | Hardwick Caldwell (VES) | | 140 | Hunter McDonald (St.Christopher's) |
| 145 | Chris Wilcox (Virginia Episcopal) | | 145 | Josh Moses (St.Christopher's) |
| 152 | Bose Bratton (Woodberry Forest) | | 152 | Will Gordon (Virginia Episcopal) |
| 160 | Ryan Robertson (St.Christopher's) | | 160 | Hardwick Caldwell (Virginia Episcopal) |
| 171 | Kirk Adamson (St.Christopher's) | | 171 | Thomas Hovis (St.Christopher's) |
| 189 | Conner Gentil (Woodberry Forest) | | 189 | Ryan Robertson (St.Christopher's) |
| 215 | Tyler Schmidt (St.Christopher's) | | 215 | Tyler Schmidt (St.Christopher's) |
| HWT | Jeb Pinkerton (St.Christopher's) | | HWT | Marcos Maldanado (Virginia Episcopal) |
| 2005 | | | 2006 | |
| 103 | Robert Fridell (Collegiate) | | 103 | Michael Blair (Collegiate) |
| 112 | Joseph Munno (St.Christopher's) | | 112 | Nick Molloy (St.Christopher's) |
| 119 | Tyler Hamblin (St.Christopher's) | | 119 | Tyler Hamblin (St.Christopher's) |
| 125 | Ryan Amorosso (Norfolk Academy) | | 125 | Tyrek Jones (Woodberry Forest) |
| 130 | Sam Redd (St.Christopher's) | | 130 | Kevin Donahue (St.Christopher's) |
| 135 | Zack Rolfe (St.Christopher's) | | 135 | Joseph Munno (St.Christopher's) |
| 140 | David Schafer (St.Christopher's) | | 140 | Taylor Emerson (Collegiate) |
| 145 | Hunter McDonald (St.Christopher's) | | 145 | Craig Philip (St.Christopher's) |
| 152 | Gianni Freeo (Virginia Episcopal) | | 152 | Will Moore (St.Christopher's) |
| 160 | Hardwick Caldwell (Virginia Episcopal) | | 160 | Zach Rolfe (St.Christopher's) |
| 171 | Hunter Higginbotham (Virginia Episcopal) | | 171 | Thomas Price (Collegiate) |
| 189 | Tyler Schmidt (St.Christopher's) | | 189 | Andy Wilson (Christchurch) |
| 215 | Jack Zampolin (St.Christopher's) | | 215 | Ashton Gilmore (St.Christopher's) |
| HWT | Tim Rose (St.Christopher's) | | HWT | Jake Marcey (Woodberry Forest) |
| 2007 | | | 2008 | |
| 103 | Bryan Whitt (Norfolk Academy) | | 103 | |
| 112 | Tyler Spangler (St.Christopher's) | | 112 | |
| 119 | Aaron Runzo (Norfolk Academy) | | 119 | |
| 125 | Loren Phillips (St.Christopher's) | | 125 | |
| 130 | Tyler Hamblen (St.Christopher's) | | 130 | |
| 135 | Kevin Donahue (St.Christopher's) | | 135 | |
| 140 | Matt Talbott (St.Christopher's) | | 140 | |
| 145 | Joseph Munno (St.Christopher's) | | 145 | |
| 152 | Johnny Fitzsimmons (Woodberry Forest) | | 152 | |
| 160 | Craig Phillip (St.Christopher's) | | 160 | |
| 171 | Clark Gottwald (St.Christopher's) | | 171 | |
| 189 | Adam Gillis (Woodberry Forest) | | 189 | |
| 215 | Jackson Freeman (St.Christopher's) | | 215 | |
| HWT | Jake Marcey (Woodberry Forest) | | HWT | |
